Tetrahydrofuran → HCID 68907140, compound

HRID 2111423Notes

Reaction equation

HRID 2111423 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:36])[C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:14]2[N:15]=[CH:16][C:17]3[N:23]([CH3:24])[C:22](=[O:25])[CH:21]([CH3:26])[CH2:20][N:19]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:18]=3[N:33]=2)[CH3:13])=[C:8]([O:34][CH3:35])[CH:7]=1.O1CCCC1>CO>[CH:27]1([N:19]2[CH2:20][CH:21]([CH3:26])[C:22](=[O:25])[N:23]([CH3:24])[C:17]3[CH:16]=[N:15][C:14]([N:12]([CH3:13])[C:9]4[CH:10]=[CH:11][C:6]([C:5]([OH:36])=[O:4])=[CH:7][C:8]=4[O:34][CH3:35])=[N:33][C:18]2=3)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 68905377HCID 68905377, compound

Product 1

HCID 68907140HCID 68907140, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of sodium hydroxide (2N, 1.0 mL, 2 mmol) was added A mixture of 0.170 g (0.00036 mole) of (rac)-4-[(9-cyclohexyl-5,7-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)-methyl-amino]-3-methoxy-benzoic acid methyl ester, 6 mL of tetrahydrofuran, 2 mL of methanol and 1 mL of 2M sodium hydroxide was heated at 75 degrees for 4 hours. The mixture was concentrated under reduced pressure and then azeotroped with toluene and concentrated under reduced pressure, The solid residue was triturated with ethyl acetate. The solid was then suspended in water and treated with 1M hydrochloric acid to pH=4. After stirring 30 minutes, the solid was collected, washed with water and dried to give 0.080 g of (rac)-4-[(9-cyclohexyl-5,7-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)-methyl-amino]-3-methoxy-benzoic acid as white powder.

Workup

  1. temperaturewas heated at 75 degrees for 4 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customazeotroped with toluene
  4. concentrationconcentrated under reduced pressure
  5. customThe solid residue was triturated with ethyl acetate
  6. additiontreated with 1M hydrochloric acid to pH=4
  7. customthe solid was collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-e7f5cfcee5cc4ebc9ccfd7d388e88016
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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